Imidazole → Isoquinoline

HRID 649149Notes

Reaction equation

HRID 649149 reaction equation
COS([O-])(=O)=O.CC1N=[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][N:11]2C=1C[N+](C)(C)C.N1C=CN=C1>C(O)C>[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 13821866HCID 13821866, compound

Product 1

HCID 8405IsoquinolineYield 144.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (4.5 g) and imidazole (2.02 g) in ethanol (45 ml) was refluxed with stirring for 7 hours and evaporated in vacuo. To the residue was added water and the resulting precipitates were collected by filtration and recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(1-imidazolylmethyl)-2-methylimidazo2,1-a]isoquinoline (2.3 g).

Workup

  1. temperaturewas refluxed
  2. customevaporated in vacuo
  3. additionTo the residue was added water
  4. customthe resulting precipitates
  5. filtrationwere collected by filtration
  6. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-e4d35951b1db4f67bc33ffff69b4dbba
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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